S, N double rearrangement. 2. X-ray crystal structures of rearranged products

M Yokoyama, M Nakamura, H Ohteki…

Index: Yokoyama, Masataka; Nakamura, Masaki; Ohteki, Hiroko; Imamoto, Tsuneo; Yamaguchi, Kei-ichi Journal of Organic Chemistry, 1982 , vol. 47, # 6 p. 1090 - 1094

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Citation Number: 19

Abstract

In the course of the syntheses of 1, 3-thiazines and related compounds, we found an interesting condensation reaction which involved a novel rearrangement. Thus, 2-cyano-3- mercapto-3-(methylthio) acrylamide (1) reacted with benzoic acid in the presence of polyphosphate ester (PPEY to give 5-carbamoyl-4-(methylthio)-2-phenyl-1, 3-thiazin-6-one (9). 3 The structures of 9 and its 2, 3-dihydro derivative 10 were unequivocally determined ...